


Please Please Me

by KarinaMay



Series: Learning Curve [2]
Category: Critical Role (Web Series)
Genre: Blow Jobs, Developing Relationship, F/M, First Time Blow Jobs, Porn with Feelings, Restraints, Smut, a teeny bit of domesticity, aka Jester has a tail and she finds a use for it, and a side helping of supportive friend, but let's be real it's mostly just smut, consent and healthy communcation, set during 115, with a tiny bit of fluff
Language: English
Status: Completed
Published: 2020-11-12
Updated: 2020-11-12
Packaged: 2021-03-10 04:22:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,343
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27528367
Author URL: https://archiveofourown.org/users/KarinaMay/pseuds/KarinaMay
Summary: “I want to try something,” Jester said. She was lying on her back on the couch, her feet dangling playfully over one of the arms. She’d disregarded her sketchbook eight minutes ago, put it down on the floor together with her charcoal and she’d been watching Caleb."What's that?" Caleb asked.“I want to try something,” she repeated. “You see, Caleb, I think I noticed something yesterday, and I want to know if I was right.”Jester is still new to the whole sex thing, butveryeager to learn. She figures out quite a successful way to keep Caleb from distracting her while she continues to find out what he likes.Part 2 of my Learning Curve series, but can be read on its own.
Relationships: Jester Lavorre & Caleb Widogast, Jester Lavorre/Caleb Widogast
Series: Learning Curve [2]
Series URL: https://archiveofourown.org/series/2012047
Comments: 10
Kudos: 128





	Please Please Me

Caleb had settled on the couch in his sitting room again, continuing his reading after quite a lively dinner. It had been a strange day all things included, and Caleb was glad to have a moment to catch his breath. There was a knock on his door and he smiled to himself. 

“Ja, come in!” he called out as he closed his book. 

It wasn’t Jester who appeared through the door. It was Beau. 

“Oh, hello Beauregard, what can I do for you?” Caleb asked, trying not to look disappointed. 

“Expecting someone else?” she asked innocently, walking over. Her ability to read him was hit or miss, but today it seemed to be right on target. 

“No, no, I was just fixing to go to bed,” Caleb said, putting his book on the side table. “It’s been a long, strange day, wouldn’t you agree?”

Beau grinned. “Definitely very strange, Caleb. Kind of a wild ride, honestly, fighting yeti’s and then ending up inviting them for dinner. Not to mention the fact you slept with Jester.”

Caleb nearly choked on his hot chocolate. “How’d you-”

“Oh my fucking _gods_ ,” Beau exclaimed almost at the same time. “I didn’t actually know _,_ I _guessed._ But it’s actually true?!”

Caleb didn’t respond, busying himself wiping the hot chocolate from his chin instead while he felt himself turn bright red.

“Wow, man, that’s - it’s weird that it makes sense, you know.”

Caleb, who finally managed to get his composure back just a little, looked up at her. "Please don’t tell the others yet. We’re trying to figure out what’s going on ourselves.”

“Oh shit,” Beau replied. “It’s _real_ serious then. Well, you know I’ll keep your secrets Caleb; I’ve done it before.”

There was another knock on the door, followed by Jester’s singsong voice. “Cay-leeeeb?” 

Beau smirked. “And that is definitely my cue to leave. But good for you man.”

Jester pushed through the door, and Beau brushed by her on her way out. 

“Hey Jessie,” she said, still grinning. “Have fun.”

The door shut behind her and Jester looked at Caleb questioningly. 

“She guessed,” Caleb said, shrugging. “She said she won’t tell the others, though.”

Jester was standing halfway between the door and the couch, hands clasped together in front of her, tail swishing nervously behind her legs. When Caleb locked his eyes on hers she bit her lip and looked away in an uncharacteristic display of shyness. They’d all but avoided each other most of the day, though Caleb at least had perhaps stolen a few too many glances at her when he thought no one had been looking. 

“How does this work, Caleb?” Jester asked. 

Caleb smiled. “Which part?”

“I don’t know…”

Caleb got up from the couch and walked over to her, reaching for her wringing hands. She clasped them around his gratefully, seemingly relaxing a bit at the contact. She’d always been a physically affectionate person; it had taken a while for Caleb to get used to at the start. It was very welcome now, though, after having kept away from her all day. Now that it had been established that he could in fact touch her, _not_ doing it had been difficult. 

“It’s a bit weird,” Jester said, smiling apologetically. 

“It is,” Caleb agreed. He dipped forward, slowly, giving her time to react. She leaned into him, meeting him halfway in a soft kiss. She sighed happily as Caleb slid his arms around her waist, relaxing against him. 

“Can I stay here again tonight?” she asked softly.

Caleb leaned back a little to look her in the eyes again. “Of course. Whenever you want.”

* * *

“I want to try something,” Jester said. She was lying on her back on the couch, her feet dangling playfully over the side. She’d disregarded her sketchbook eight minutes ago, put it down on the floor together with her charcoal and she’d been watching Caleb. Studying him while he studied some really dense text about the history of dunamantic magic. He should really be interested in it, but he’d noticed her eyes on him as soon as her attention had turned and he’d read page 293 at least three times over now, and for someone with near perfect memory, he was having a hard time retaining any of the information. 

He looked up at her when she spoke. “What’s that?”

He noticed the familiar mischievous look in her eyes, her tail swishing playfully in the air. “I want to try something,” she repeated. “You see, Caleb, I think I noticed something yesterday, and I want to know if I was right.” 

Caleb closed the book and gingerly put it down on the side table next to his chair. “Right about what?” he asked. 

She pushed herself upright on the couch, legs still hanging off the side. Her skirt had pooled around her thighs, just revealing the ribbons holding up her knitted stockings. Pretty ribbons, pretty stockings. Caleb very much wanted to take them off of her. She grinned at him and kicked her legs a few times.

“What’re you looking at, Caleb?” she asked, feigning innocence. 

“You,” Caleb answered, as he got up out of his chair. 

She flung her legs off the side of the couch, climbing onto his lap immediately when he sat down next to her. She looked down at him now with that same spark in her eyes as she slowly, deliberately ran her hands up her thighs, pulling up the fabric of her skirt even higher, toying with the pale blue ribbons that matched her skin.

“Pretty, right?” she asked. 

Caleb’s eyes were locked on her fingers as they teased at the edge of her stockings, but he could tell that she was smiling again, just from the sound of her voice. 

“Ja,” Caleb replied. “Is that what you noticed yesterday? That I like your legs?”

“Oh, I definitely may have noticed that as well,” Jester said. “But I was thinking about something else, actually.”

“And are you going to tell me, Schatz?”

“Maaaaybe.” 

Caleb chuckled and shook his head. He reached for her hands - or rather, her thighs - but she snatched his hands out of the air, wrapping them around her waist instead, leaning into him for a kiss. She slid both her hands into his hair, pulling him closer harsh enough that Caleb gasped into her mouth. A familiar heat was already gathering in the pit of his stomach and he fisted his hands into the fabric of her dress, pulling her flush against his chest. 

Her curiosity from the night before was still there as she ran her hands from his hair down his chest, exploring every bit of him she could reach, but she was less hesitant now, more sure of herself. She quickly popped open the few buttons of his shirt and ran her nails over his chest. Caleb groaned into her mouth at the sharp sting, and he rolled his hips up into hers.

Caleb slid his hands from her back to her stomach and started feeling his way down to her core when suddenly something wrapped tightly around his wrists, leaving his hands suspended in the air between them. Caleb’s eyes snapped open as Jester pushed herself off of his chest and glanced down with a smirk. Caleb followed her gaze and swallowed hard when he saw her tail wrapped around his wrists, tight enough to sting, certainly tight enough to leave marks. She was restraining him, but she still had both her hands free to do whatever she pleased. 

“Was I right?” Jester asked, brushing her fingers over her own tail around his arms. “You like this?”

“Ja,” Caleb breathed. 

“That’s fun,” Jester said softly, playfulness back on her face. She pushed herself up from his lap, off of the couch and knelt between his legs in front of him, firmly keeping his hands tied together. “It’ll be much easier to figure you out when you aren’t distracting me all the time.”

Caleb’s laugh turned into a moan when her hands dropped to the laces of his pants. Her featherlight touches unlacing them did nothing to relieve the tension steadily building there, but when he bucked his hips forward, desperately searching for _more_ , her hands flew off him entirely. 

She clicked her tongue at him. “You need a lesson in patience, Caleb.”

“Jester,” Caleb groaned her name. "You're going to kill me, aren't you?"

She grinned but didn't answer. Her hands landed back on his hips, hooking her fingers under the hem of his pants. “Lift?” she asked. Caleb obliged, lifting his hips from the couch enough for her to slip them down his legs. She tugged a little at his hands with her tail then, locking her eyes on his. “Tell me if I need to let go, yes?”

Caleb nodded shakily. 

“Good,” she said. “Now like I said yesterday… Don’t try to keep quiet, I want to know when it feels good.”

Caleb opened his mouth to reply, but suddenly her soft, wet lips were on his inner thigh, sucking a bruise into his skin and a moan fell from his lips instead, and another one when she dragged her sharp teeth over the sensitive spot she’d made. Seemingly satisfied with the noises he was making, she continued an agonizingly slow path up his thigh, kissing and sucking colourful bruises onto his pale skin. 

Caleb was trembling, his cock already hard now, begging for any kind of touch. “Jester, _please_ ,” he choked out, hands tensing against their restraints. 

She looked up at him, eyes wide, pupils blown. “Pretty,” she mumbled, before speaking up slightly. “Please what, Caleb?”

“Touch me,” Caleb breathed. “Please touch me, Jester.”

“I like it when you ask so sweetly,” she said. She planted her hands more firmly on his thighs, keeping him in place as she moved closer to him. With her tail she guided his hands around her neck, resting his wrists on her shoulder. He still wasn’t actively touching her, but he felt steadied somewhat being allowed to lean on her, and the new positioning of his hands made her hold on his wrist tighten some more, the sharp, stinging sensation sending another wave of pleasure down his spine. 

She dipped forward and placed a wet kiss at the base of his erection and then licked a stripe up to the tip, swirling her tongue around it, tasting him. Caleb’s mouth fell open and he let out another moan, louder than before, as his head fell back against the back of the couch. She wrapped her lips around the tip, and bobbed her head, slowly, careful as she figured out something new. Around halfway down his length she hollowed her cheeks and sucked back up.

“Gods, Jester,” he groaned, as she started setting a rhythm, familiarizing herself with the feeling of him and taking him down a bit further every time. With considerable effort Caleb pushed his head back up from the back of the couch to look down at her and nearly came apart just from the sight of her between his legs, full lips wrapped around his cock, violet eyes locked on his face trying to read his every expression, every noise. 

And Caleb was _loud._ For someone who was figuring out how to do this for the first time, Jester was sinfully good at it - which in all honesty, Caleb should’ve expected given the previous night. 

“Gods, you’re perfect,” he managed between moans. She hummed around him happily and the added vibration made the heat in Caleb’s stomach coil up, his muscles tensing. “I’m not - fuck - I’m not going to last very long.”

Something sparked in her eyes and she hummed again. Caleb involuntarily jerked his hands, pulling her closer, and for a split second concern took over as she made a small choking noise. Then she swallowed around him, adjusting her throat to the feeling and taking him down a little further again. She picked up her rhythm again, faster now, swallowing him down with more and more ease, eyes closing and moaning softly in time with him. It was tight and wet and wonderful and rapidly becoming too much to handle. 

“Jester please I’m - I’m going to-”

She moaned around him again as he came down her throat, swallowing again and again, working him through the waves of his orgasm. 

She eventually slipped her mouth off of him with an obscene _pop_ and smiled up at him. She licked her lips and released his hands from her hold.

“Good?” she asked innocently.

Caleb closed his eyes for a moment, shaking his head. “Ja, good,” he answered. “Definitely good. Better than good, really.”

She pushed herself up so she was back at eye level with him. He brought his hands up to cup her face and she turned her head to kiss his palm, glancing at the angry red welt on his wrist. 

“Does it hurt?” she asked. “In a bad way, I mean?”

Caleb shook his head. “No, only in a good way.”

She pressed a quick kiss against the irritated skin and Caleb sucked in a sharp breath. Jester turned to face him again. “That’s pretty hot, you know.”

Caleb smirked. “Is that so, liebling?”

“Yeah it really is,” she replied. “And who knew you looked so pretty saying ‘please’?”

“In that case, can I _please_ kiss you now?”

She nodded and Caleb leaned forward, capturing her lips with his own and lazily slipping his tongue into her mouth. He could still taste himself on her tongue, and there was something strangely intoxicating about how it mixed with her own taste. 

Without a warning she jumped up, startling him. 

“Come on,” she said brightly. “Let’s get you cleaned up. And then afterward maybe you can please _me_.”

She skipped away to his bedroom and Caleb ran his hands over his face and got up from the couch to follow her. She was going to be the death of him for sure, but he couldn’t think of a better way to go. 

**Author's Note:**

> And I'm back! Thanks to everyone who left lovely comments on Uselessly Devoted, if it weren't for those I probably wouldn't have written this one. 
> 
> However, now we've established this is in fact a series of sinful oneshots, I can tell you there's another one coming up soon. Bathtime shenanigans, anyone?
> 
> Anyway, feel free to come yell at me here in the comments or on [twitter](http://twitter.com/isacosplay) or [tumblr](http://mskarinamay.tumblr.com), I love hearing from y'all. 
> 
> Thanks for reading!
> 
> -X


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